Trifluoroacetic acid → HCID 68298571, compound

HRID 2271948Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[C:4]([C:10]2[CH:11]=[C:12]3[C:17](=[CH:18][CH:19]=2)[N:16]=[CH:15][C:14]([C:20]([CH:22]2[CH2:24][CH2:23]2)=[O:21])=[C:13]3[NH:25][C:26]2[CH:31]=[CH:30][C:29]([C:32]([NH:35]C(=O)OC(C)(C)C)([CH3:34])[CH3:33])=[CH:28][CH:27]=2)[CH:5]=[C:6]([F:9])[C:7]=1[OH:8].C(O)(C(F)(F)F)=O>>[NH2:35][C:32]([C:29]1[CH:28]=[CH:27][C:26]([NH:25][C:13]2[C:12]3[C:17](=[CH:18][CH:19]=[C:10]([C:4]4[CH:5]=[C:6]([F:9])[C:7]([OH:8])=[C:2]([Cl:1])[CH:3]=4)[CH:11]=3)[N:16]=[CH:15][C:14]=2[C:20]([CH:22]2[CH2:23][CH2:24]2)=[O:21])=[CH:31][CH:30]=1)([CH3:34])[CH3:33]

Participants

Reactant 2

HCID 6422Trifluoroacetic acid

HCID 86692989HCID 86692989, compound

Product 1

HCID 68298571HCID 68298571, compoundYield 32.1%

Procedure

Following general procedure A-2, tert-butyl 2-{4-[6-(3-chloro-5-fluoro-4-hydroxyphenyl)-3-(cyclopropanecarbonyl)quinolin-4-ylamino]phenyl}propan-2-ylcarbamate (0.140 mmol) was reacted with TFA (2 mL) to afford the desired product (22 mg, 32% over two steps) as a yellow solid: 1H NMR (500 MHz, CD3OD+TFA-I) δ 9.38 (s, 1H), 8.26 (dd, J=8.9, 1.9 Hz, 1H), 8.12 (s, 1H), 8.05 (d, J=8.8 Hz, 1H), 7.69 (d, J=8.0, 2H), 7.54 (d, J=8.0 Hz, 2H), 7.30 (t, J=1.9 Hz, 1H), 7.10-7.03 (m, 1H), 2.84-2.76 (m, 1H), 1.79 (s, 6H), 1.19-1.12 (m, 4H).; ESI MS m/z 490 [C28H25ClFN3O2+H]+; HPLC>99% (AUC), tR=10.80 min.

Sources & evidence

ORD record: ord-b95857c6044b4d709de73b1e70e98bd9
Source dataset: uspto-grants-2015_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09120749B2

Reaction notes

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